Lipozyme TL IM-catalyzed Esterification of Oleic Acid for 1,3-Diacylglycerol Preparation†

doi:10.7503/cjcu20141106

Abstract

Abstract:

The potential of using lipase Lipozyme TL IM-mediated esterification of oleic acid with monoglyceride for 1,3-dioleoylglycerol(DO) preparation was explored and the effects of solvent, water activity, temperature, molar ratio of oleic acid to monostearin(MO) and the solvent quantity on the DO yield and 1,3-positional selectivity of the lipase were investigated systematically. Under the optimum conditions(45 ℃, 1.5 g of Lipozyme TL IM, molar ratio of oleic acid to MO is 1.5∶1, 6.0 g chloroform, and water activity is 0.33), a total DO yield of 80% could be achieved with the content of 1,3-DO over 92%. Lipozyme TL IM showed rather good operational stability in the system and there was no obvious reduction in lipase’s activity and selectivity even after being continually used for 5 batches.

Key words: Lipozyme TL IM, Oleic acid, Monoglyceride, 1, 3-DAG, Positional selectivity

CLC Number:

TrendMD:

WANG Zitian, SU Jianxiao, DU Wei, DAI Lingmei, LIU Dehua. Lipozyme TL IM-catalyzed Esterification of Oleic Acid for 1,3-Diacylglycerol Preparation^†[J]. Chem. J. Chinese Universities, 2015, 36(8): 1535.

Figures/Tables 7

Table 1 Gradient elution programa

Time/min	V(Dichloromethane)∶V(Acetonitrile-acetic acid)^b
0	0∶100
4	0∶100
12	10∶90
25	10∶90
30	30∶70
35	30∶70
45	80∶20
55	80∶20
60	0∶100
65	0∶100

Fig.1 Effects of solvents on DO yield(A) and positional selectivity(B) during esterificationn(OA)∶n(MO)=1.5∶1, water activity=0.53, 45 ℃, 15%(mass ratio) enzyme to OA, 200 r/min,3 g molecular sieve. a. Acetone; b.t-butanol; c. chloroform; d. n-hexane.

Fig.2 Effects of water activity on DO yield(A) and positional selectivity(B) during esterificationn(OA)∶n(MO)=1.5∶1, 20%(mass fraction) chloroform, 45 ℃, 15%(mass ratio) enzyme to OA, 200 r/min, 3 g molecular sieve. Water activity: a. 0.11; b. 0.33; c. 0.53; d. 0.75; e. 0.97.

Fig.3 Effects of temperature on DO yield(A) and positional selectivity(B) during esterificationn(OA)∶n(MO)=1.5∶1, 20%(mass fraction) chloroform, water activity: 0.33, 15%(mass ratio) enzyme to OA, 200 r/min, 3 g molecular sieve. Temperature/℃: a. 45; b. 55; c. 60.

Fig.4 Effects of molar ratio of oleic acid to monoglycerid on DO yield(A) and positional selectivity(B) during esterification20%(mass fraction) Chloroform, water activity: 0.33, 45 ℃, 15% enzyme, 200 r/min, 3 g molecular sieve.n(OA)∶n(MO): a. 1∶1; b. 1.2∶1; c. 1.5∶1; d. 2∶1.

Fig.5 Effects of solvent quantity on DO yield(A) and positional selectivity(B) during esterificationn(OA)∶n(MO)=1.5∶1, chloroform, water activity: 0.33, 45 ℃, 15% enzyme, 200 r/min, 3 g molecular sieve. Mass fraction of solvent: a. 20%; b. 40%; c. 60%; d. 80%.

Fig.6 Operational yield(A) and selectivity(B) of Lipozyme TL IM during the esterification Reaction conditions: n(OA)∶n(MO)=1.5∶1, 60% chloroform, water activity: 0.33, 45 ℃, 15% enzyme, 200 r/min, 3 g molecular sieve.

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